I think this is quite hard job being a parents... to wane a child from something they are used to do or shall we say on their habits. For our experienced waning Jaden from his pacifier was just so easy. We had no worries too when we trained him pooping in the toilet. Though he can't sit on the toilet bowl by himself but the idea that he can tell us that he needs to go to the toilet. He never did poop in his diaper since then but still we put on diaper because he can't tell us yet if he needs to pee.
I am not so sure when is the right time to wane a child from bottle feeding. We are now planning to wane him in bottle feeding and we tried to introduce him drinking his milk with a glass. Last two night ago, I did try feeding him at night with a glass of milk but he drink a few sipped and never did again. It was really a different thing for him to drink his milk with a glass. Hoping that sooner he will get used of it.